Water → HCID 58109481, compound

HRID 884360Notes

Reaction equation

HRID 884360 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([OH:28])([CH2:25][CH:26]=[CH2:27])[CH2:9][CH2:10][NH:11][C@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:13]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[C:37](Cl)([O:39]C(=O)OC(Cl)(Cl)Cl)Cl.O>C(Cl)Cl>[CH2:25]([C:8]1([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)[O:28][C:37](=[O:39])[N:11]([C@H:12]2[CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20][C:21]([CH3:23])([CH3:24])[CH3:22])=[O:19])[CH2:13]2)[CH2:10][CH2:9]1)[CH:26]=[CH2:27]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 94429TriphosgeneHCID 58109526HCID 58109526, compound

Product 1

HCID 58109481HCID 58109481, compoundYield 39.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3S)-tert-butyl 3-(3-(4-fluorophenyl)-3-hydroxyhex-5-enylamino)-piperidine-1-carboxylate (500 mg, 1.27 mmol) and triethylamine (515 mg, 5.1 mmol) in dried methylene chloride (13 mL) at 0° C. was added triphosgene (126 mg, 0.42 mmol). The mixture was stirred at room temperature till the reaction was over. Water was added, and the layers were separated. The aqueous layer was extracted with methylene chloride. The combined organic layer was washed with water, dried over Na2SO4, and condensed to give the crude product, which was purified by column chromatography on silica gel to afford (3S)-tert-butyl 3-(6-allyl-6-(4-fluorophenyl)-2-oxo-1,3-oxazinan-3-yl)piperidine-1-carboxylate (70 mg, 13%). 1H NMR: (CDCl3): 1.37 (d, 9H), 1.43 (m, 1H), 1.64 (m, 1H), 2.22 (m, 2H), 2.64 (m, 5H), 3.11 (m, 1H), 3.91 (broad, 3H), 5.00 (q, 2H), 5.65 (m, 1H), 6.99 (t, 3H), 7.20 (m, 2H).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with methylene chloride
  3. washThe combined organic layer was washed with water
  4. dry with materialdried over Na2SO4, and condensed
  5. customto give the crude product, which
  6. customwas purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-45d82f783be7430d88b6ef53da013092
Source dataset
uspto-grants-2012_08
Patent number
US08242111B2

Reaction notes

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